<i>Per</i>-C-6 Oligosaccharide-Branched Cyclodextrin Interacting with Both the Lectin and Drug

Yasuda, Naoyoshi; Aoki, Nobuyoshi; Abe, Hideyoshi; Hattori, Kiyohiko

doi:10.1246/cl.2000.706

Cited by 20 publications

(14 citation statements)

References 14 publications

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“…The authors hypothesized that the mono-Lac-aCD conjugate 79 should thread onto the polymer chain in aqueous solution and rest preferentially on the hydrophobic decamethylene segments (83), which was confirmed by 1 H NMR Scheme 33 Mal-aCD-PRX-coated polystyrene microspheres.…”

Section: -125mentioning

confidence: 95%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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Section: -125mentioning

confidence: 95%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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“…22) Figure 2 indicates the kinetic linear plots of 5 and 6. The association rate constant (k a ) and dissociation rate constant (k d ) of 5 (or 6) were 1.4ϫ10 4 Fig. 3.…”

Section: Resultsmentioning

confidence: 96%

“…These K a values are remarkably high when compared with the inclusion association of the lactose-b-CyD conjugate 4 4) or normal b-CyD which was on the order of 10 3 M…”

mentioning

confidence: 94%

“…5) The CyD derivatives attached to saccharide moieties are expected to carry drug molecules to specific cells, because they have both the drug-inclusion ability of CyDs and the cell-recognition of saccharides. 4,[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] Then, our next objective was the synthesis of a novel b-CyD conjugate having another hydroquinone glycoside. This paper describes the synthesis of two novel b-CyD derivatives attached to a hydroquinone glycoside containing an a-D-glucopyranosidic or 2-acetamido-2-deoxy-a-D-glucopyranosidic linkage and the evaluation of their DXR-inclusion abilities.…”

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confidence: 99%

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Syntheses and Doxorubicin-Inclusion Abilities of .BETA.-Cyclodextrin Derivatives with a Hydroquinone .ALPHA.-Glycoside Residue Attached at the Primary Side

Oda

Miura

Hattori

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Our recent study showed that the b-glucose-b-cyclodextrin (CyD) conjugates 1 and 2 as shown in Fig. 1 were successfully prepared from b-CyD and arbutin (4-hydroxyphenyl b-glucopyranoside, 3). [1][2][3] Arbutin 3 is a naturally occurring hydroquinone glycoside containing a b-D-glucosidic linkage. An appropriate linker necessary to connect 3 with a b-CyD derivative was conveniently introduced into the phenolic alcohol of 3. The inclusion association constants (K a ) of 1 and 2 for the immobilized doxorubicin (DXR, anticancer agent) measured using a surface plasmon resonance (SPR) optical biosensor were 10 5 -10 6 M Ϫ1. These K a values are remarkably high when compared with the inclusion association of the lactose-b-CyD conjugate 4 4) or normal b-CyD which was on the order of 10 3 M Ϫ1. The b-CyD derivatives 1 and 2 were characterized by the existence of the phenyl group in the spacer between the glucose and b-CyD. The p-p stacking interaction effect between the phenyl group and DXR would increase their inclusion associations for DXR.3) Thus, our former study showed that the hydroquinone glycoside could be a synthetically useful component for providing a saccharide-b-CyD conjugate which is expected to have an excellent DXR-inclusion ability. 5)The CyD derivatives attached to saccharide moieties are expected to carry drug molecules to specific cells, because they have both the drug-inclusion ability of CyDs and the cell-recognition of saccharides. 4,[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] Then, our next objective was the synthesis of a novel b-CyD conjugate having another hydroquinone glycoside. This paper describes the synthesis of two novel b-CyD derivatives attached to a hydroquinone glycoside containing an a-D-glucopyranosidic or 2-acetamido-2-deoxy-a-D-glucopyranosidic linkage and the evaluation of their DXR-inclusion abilities. Results and DiscussionWe designed two novel b-CyD derivatives 5 and 6 attached to a hydroquinone glycoside containing an a-D-glucosidic or 2-acetamido-2-deoxy-a-D-glucosidic linkage as shown in Fig. 1.Chart 1 shows the synthetic procedure of 5 using 4-hydroxyphenyl a-glucopyranoside (a-arbutin, 7). The reaction of allyl bromide (1.2 eq) with the dry sodium salt of 7 in N,N-dimethylformamide (DMF) for 70 h gave the allylated compound 8 in 84% yield. The benzylation of 8 using benzyl bromide (4.8 eq) and NaH (16 eq) in DMF for 21 h afforded compound 9 in 99% yield. The hydroboration of 9 with 9-borabicyclo[3.3.1]nonane (9-BBN) (2 eq) in tetrahydrofuran (THF) at 0°C for 5 h, followed by oxidation using aq. H 2 O 2 (10 eq) and by hydrolysis with aq. NaOH (3 eq) for 48 h gave compound 10 in 94% yield. The iodination of 10 with iodine (4 eq) in the presence of Ph 3 P (4 eq) in DMF at 35°C for 2 h quantitatively gave compound 11 in 89% yield. The condensation of 11 (3.8 eq) with the benzylated b-CyD 12 23) using KOH (ca. 120 eq) and tetra-n-butylammonium iodide (nBu 4 NI) (0.5 eq) in DMF for 64 h gave 13 in 69% yield. The treatment of 13 with H 2 -Pd(OH) 2 in DMF for ...

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“…Yasuda et al [14] have reported the synthesis of per-6galactosyl-glucono-amide-CD 12 and its monovalent analogue 13 (Fig. 3) by nucleophilic displacement of halogen-β-CD.…”

Section: Per-substituted Cyclodextrins On a Facementioning

confidence: 99%

Editorial (Thematic Issue: The Role of Reactive Oxygen Species in Organ Pathologies Due to Drugs Abuse: Do We Have the Culprit?)

Turillazzi¹

2013

MROC

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This review concentrates on both the protein receptor and guest binding abilities of carbohydrate clusters based on a cyclodextrin core. The combination of both complexation abilities is the basis of one of the pursued approaches for developing site-specific drug delivery systems. Influence on the molecular recognition properties of the number of appended saccharides, the type of carbohydrate clustering and the type of the spacer arms, among other factors, are discussed.

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Per-C-6 Oligosaccharide-Branched Cyclodextrin Interacting with Both the Lectin and Drug

Abstract: The improved dual interactions with both the lectin (PNA, a cellular receptor model) and an anticancer drug (DXR) have been observed in per-C-6 oligosaccharide-branched cyclodextrin (2) using an optical biosensor based on SPR.

Cited by 20 publications

References 14 publications

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Syntheses and Doxorubicin-Inclusion Abilities of .BETA.-Cyclodextrin Derivatives with a Hydroquinone .ALPHA.-Glycoside Residue Attached at the Primary Side

Editorial (Thematic Issue: The Role of Reactive Oxygen Species in Organ Pathologies Due to Drugs Abuse: Do We Have the Culprit?)

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